


Casual Encounter

by sleepypercy



Category: Supernatural
Genre: Although I don't think Sam likes labels so much, M/M, Online Dating, Sam In Panties, Transvestite, underage if you're american
Language: English
Status: Completed
Published: 2017-09-28
Updated: 2017-09-28
Packaged: 2019-01-06 10:05:57
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,366
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12209043
Author URL: https://archiveofourown.org/users/sleepypercy/pseuds/sleepypercy
Summary: Dean stumbles on Sam's online dating profile. It's a bit... sluttier than he would have expected.For PrettySlutBoys for letting me go on about Sam in panties ♥Unbeta'd and written in a night, so my apologies if it's a little rough. I'll try to go through once my head is clear and check for typos and mistakes.





	Casual Encounter

**Author's Note:**

  * For [PrettySlutBoys](https://archiveofourown.org/users/PrettySlutBoys/gifts).



It’s been a long day and Dean just wants to crawl into bed and let his muscles relax. He’d lost count of how many cars he’d worked on. Changing oil, replacing brake pads, taking apart engines and replacing parts that car manufacturers made too damn hard to reach.

As soon as he gets home, however, Sam’s there, SAT books and printed off study guides spread all over the table. Sam’s bent over it all, intense look in his eye that Dean knows better than to interrupt. The test is in two weeks, and Sam had insisted that their dad let them stay in one place so he could actually sign up and take the test. So John had dropped them off with Uncle Bobby who had insisted that Dean stick around as well.

Bobby’s always been like that. He doesn’t quite agree with John’s lifestyle (especially the part where he drags his children all over the goddamn country), and has never really hidden his feelings. But he’s always been there for John when he needed him, and he’s always tried to give the boys as much normalcy as he could offer.

Bobby’s not home, so Dean heads to the kitchen to figure out what to make for dinner. He’s certain Sam hasn’t started anything. The boy could burn water. He doesn’t have the energy to make anything complicated, and he’s thankful to find a frozen pizza that he can throw in the oven.

While he’s waiting for the pizza to cook, Dean boots up his laptop, kicks his feet on on a chair, and browses the depths of the internet.

Sam wanders in a little while later, no doubt lured in by the smell of bubbling cheese and crisping sausage. Dean doesn’t even hear him come in until Sam’s voice shrieks behind his ear.

“Hey–Dean! Dude! Do you have to do that here?”

Dean jumps in surprise before turning to toss a grin Sam’ way, reaching out to smack him on the arm and chuckling.

“What? I mean, I know you’re pretty much a monk, but I’m sure you’ve seen a pair of tits before.”

“We _eat_ on this table,” Sam protests, looking down with unhidden disgust.

“I’m not doing anything,” Dean replies, hands held up as proof, although he can’t help adding a sly, “yet,” just to see Sam’s disgust deepen. “Just shopping right now, Sammy. You should try it. Might do you some good to find a casual encounter. Maybe even loosen up some of that test-taking tension.”

Dean waits a beat, watching Sam’s mouth open to give some scathing reply, but Dean jumps back in before Sam can say a word. “Ah, nevermind. You’d have to find the key to your chastity belt first.”

“Just because I don’t leave my porn out for everyone to see–” Sam starts, but Dean interrupts before his brother’s tirade can go too far.

“Oh! So you _do_ have porn?” He grins in a way that he knows infuriates Sam. “What do you go for? Plaid schoolgirl with pigtails? Dirty librarian? One of those big wooden paddles to spank your ass?”

A heated bitchface is aimed Dean’s way just before Sam huffs and asks, “Pizza done yet?”

“Ten minutes.”

Rolling his eyes, Sam flounces out of the kitchen before Dean can say another word.

Bobby wanders in just after that and once the pizza is done, they sit around, grunting tired updates to each other until they all head up to bed.

Sam’s definitely wound up tighter than usual, and Dean’s honestly not sure why Sam’s so stressed out about this particular test. He knows his brother’s smart. Well – not just smart. Practically a genius, and it makes Dean both proud and scared at the same time. Sam’s always been too perceptive for his own good, and Dean wants to ask Sam why he cares so much about some damn test that won’t matter once Sam graduates and joins Dean full-time in the family business, but Dean’s also scared to ask.

He backs off a little the next couple of days and gives Sam some space. Even makes a few meals that weren’t originally made by Chef Boyardee or Dominos.

Of course, Dean has needs too. He’s been debating whether or not to try for a hook up while he’s in town, although it almost seems like too much work.

He’s got a casual encounter profile under a fake name but a real face. He likes browsing through the profiles, checking out pictures and knowing there’s a real person on the other end. He clicks through all varieties. He’s never been concerned with what gets him there: girl, boy, other variations with pretty parts. All mixtures of roleplay and kinks. As long as it feels good, Dean’s into it. 

He’s still debating what he wants to get into when he sees a notification in his inbox. Someone winked at him. Quickly, he clicks on their profile link, mouth watering when he sees the first picture. It’s a pair of long, lean muscled legs that lead up to a round ass peeking from underneath a short plaid skirt. A dark blue top is tied in the front to show off a flat tummy, happy trail leading down to just the barest hint of a hard-on under the skirt. Long fingers skim the front of the skirt, making Dean’s eyes rove down. He wants to wrap those long legs around his head and suck the boy off until he screams.

It doesn’t bother Dean to know he’s looking at a guy. His hook-ups have been maybe 60-40 girls/guys. He has a weakness for pretty young things, especially ones that can pull off the high knee sock look.

There’s a nice warm pressure building up in his groin just from this first picture, and Dean slips a hand under his boxers, skimming his fingers around his dick.

The second picture has the guy in all pink: rose-printed panties with a wet spot on the front. The boy’s dick is hard, pointed to the left and managing to just stay inside the cotton fabric. Pink-and-white socks come up to the boy’s tan knee, pretty bows tied at the tops, and a peachy-pink cami that lets his belly just peek out. There’s also a black string tied around the young man’s throat, tied into a tiny bow, and candy bracelets around his wrists.

The boy’s face is artfully hidden, either turned away or cut out of frame.

In the third picture the boy swaps out knee-socks for thigh-high panty hose, the kind that criss-cross in tiny black stripes. There’s another skirt, gray tweed that barely covers his ass, paired with a tucked-in collared shirt opened low in the front. The boy’s pink lips are just barely in frame, dropped low, the earpiece of one side hooked inside the wet part of his mouth and tugging it out just a bit.

Dean can just barely make out where the mounds of his ass start, so curvy and tan, and his hand speeds up, dick blurting wet. The last photo has a pair of blue boy shorts with ribbons on the front that Dean likes very much. The young guy is bent over a table, skirt pushed up around his waist and heart-shaped butt on display, long-lashed eyes just peeking over his shoulder, floppy hair held back with a sparkly barrette.

Dean’s breath starts going faster, grunting as he feels his body tense up, dick so hard and full right now. He starts thinking about everything he wants to do to that ass and mouth, how pink both of them would turn after being well used. He notices the caption on the profile, underneath an icon of an ass in pink panties: _Wanna be your dream slut._

Fuck. He clicks through the pictures again, back and forth while his dick builds up, eyes roving every perfect curve, the way the boy’s ass rounds down to his thighs, how pink his mouth is, like he’s been chewing on his own lips. Dean tries to hold off, wants to draw this out, but he can’t. He erupts in a sudden rush, lights blurring behind his eyes as he comes harder than he can ever remember coming. 

Fuck. This guy’s definitely his dream slut.

As soon as Dean’s head is clear, he wonders if he should message the guy back. Thank him for the jerk-off fodder. Maybe even suggest they meet.

It takes him all of 30 seconds to make up his mind.

_Cutest ass I’ve ever seen. Got anymore pics?_

The reply comes the next night.

_Of course. Got even better ones for friends ;-)_

It’s accompanied by a friend request, which Dean immediately accepts.

As soon as the first picture opens, his breath catches in a short gasp. It wasn’t like he hadn’t noticed the similarities before, but the angles were just distorted enough that he hadn’t been certain. 

It’s Sam. His face is in full view, and the pictures are even hotter.

It should freak him out. And it does. But it doesn’t stop how fucking turned on Dean still is. God, Sam’s so pretty and curvy like this. It had been a few years since Dean had properly seen his brother naked, other than incidental flashes around the bathroom. He had no idea when Sam had turned from a skinny little boy into this sex-curved beautiful minx.

The photos are gold. Sam’s face is in full view for most of them, tiny smirk on his lips. His poses get even sluttier, wet cock tip poking out of see-through mesh panties, tongue peeking out to lick at a gigantic dildo. But the one that stops Dean cold is the last one. Sam’s legs are wrapped up in black thigh-highs with bows at the top, and they’re spread wide open. Right between the plush rise of Sam’s cheeks is a pink plug, just the flat tip showing. The edge of Sam’s pinky finger just grazes the plug while the rest of his fingers are splayed around the base of his hard cock, pushing the panties aside.

It fucks Dean up.

He doesn’t know what Sam’s thinking, taking these. He especially doesn’t know what Sam’s thinking, sending these to Dean. But he can’t deny that his baby brother looks good. 

Sam doesn’t say a word when Dean gets home from work the next day. He’s still hunched over his testing materials, doesn’t even look up when Dean walks in.

The next few nights are spent masturbating to the same pictures. Watching Sam during dinner time, trying to catch sight of how the kid’s ass looks through his loose jeans. Remembering how round and beautiful it looked. Sam, for his part, seems oblivious, caught in testing mode, and Dean wondered how long ago Sam took those photos. A lot of them looked like different motel rooms, which all blurred together in Dean’s mind after checking into so many.

He beats off and wonders where Sam hid his stash of lingerie and skirts, and especially wonders when Sam manages to find time to pose for these dirty pictures when no one else is around. Fuck, his brother’s so dirty and sluttier than he’d ever imagined. Dean thinks Sam would fall so pretty to his knees, lips all wet and ready, hands between his own legs while he sucks his big brother’s cock. Dean comes with a long huff, chest pumping up and down in deep breaths. 

Sam’s test is Saturday and the garage hadn’t scheduled Dean for that day. He decides to go shopping.

He ends up in a high-end lingerie store. He’d be embarrassed but he’s not the only guy in the store, and the sales clerks are professional and discrete. After a good half hour, Dean finds the perfect outfit: baby blue panties with pink and white frills around the edges. There’s matching pink and blue striped knee socks, which Dean knows Sam would love. He’s not sure what to pair it with though, and it takes a while longer until Dean finds something he didn’t know he wanted until he sees it.

It’s a loose, off-the-shoulder light top. Pink. Close enough color to match the panties. The fabric is soft and pools in Dean’s hands like water, and when Dean gets really close, he can see tiny hearts, just a shade of pink lighter than the rest of the top. Sam’s tan shoulders would peek through so pretty. 

The sales clerk wraps it up really pretty in a white bag, silver tissues inside. Dean leaves it in front of Sam’s bedroom door. He adds a little note inside, scrawled on a piece of scrap paper.

_Good luck on your test. I know you did well. Thought you deserved something pretty for all your hard work._

It’s torture to wait for Sam to get home. And Dean’s not too sure how he’s brother’s going to feel when he’s done. Sam has a tendency to get snippy after a test.

When he finally hears the screen door slam, Dean goes still, listening to Sam wanders through the kitchen before padding upstairs.

He’s not sure how long it takes. Two minutes. Five. Twenty. Time stretches in weird ways until there’s a tiny knock at his door. The door opens just after that.

Sam’s standing in the doorway in the outfit Dean had just bought. God, he looks perfect. His tan skin looks so good in that color, those long legs wrapped in striped blue and pink. The loose top falls over his shoulder delicately, putting golden skin on display. There’s a mole just to the side of Sam’s collarbone that Dean really wants to kiss. Sam’s ass is pushed back against the doorframe, ruffles sliding between his body and the door. Dean can’t stop looking.

“I take it you liked all my pictures.” Sam’s eyes flutter lightly, and Dean notices his lips have a subtle shine to them.

“I did,” Dean answers immediately, pleased with the way Sam’s smile spreads. “I – fuck. Sam, you’re so fucking beautiful.”

Sam takes a step forward, socked toes quiet on the floor. He smirks. “You jerk off to my pictures, big brother?”

Dean’s quiet as Sam takes a few more steps forward. When Sam reaches the edge of the bed, he stops, expectant expression on his face.

“Thought I was gonna break my dick by the end,” Dean admits. “Hottest thing I’ve ever seen, Sammy. Barring this moment.”

“Wanna do more than just look?” Sam asks as he slides onto the bed.

“Fuck yeah,” Dean manages to whisper just before he darts forward, soft hand cupped around the back of Sam’s head as he pulls it close so he can kiss him.

Sam tastes better than Dean even imagined. And he knows how to kiss. His mouth goes soft and ripe, pink tongue peeking out to lick at Dean’s, body pressing forward until he’s pretty much in Dean’s lap.

Dean’s hands go up that soft top, fingers exploring until he gets to his brother’s pink tits. The moment he tweaks them, Sam’s head tilts back, eyes fluttering back and breath going soft. Dean takes the moment to get his mouth on Sam’s exposed collarbone, drawing warm skin in his mouth to kiss and suck. He goes along the whole side of Sam’s collar then up his neck, moving so he could whisper to the side of Sam’s ear: “Lean back, baby. Wanna suck you off.”

Sam makes some strangled noise as he complies, and Dean grins when he sees how hard his baby brother is. With his mouth he traces the shape of Sam’s dick through the panties, breathing warm and wet until Sam starts whining pathetically.

“I gotcha,” Dean assures him as he slips the panties down enough to catch the head of Sam’s dick inside his mouth.

“Dean!” Sam hiccups, arching his back up while Dean nuzzles his throat further down, taking Sam deep and swallowing wet around his warm, hard dick. Soft, stuttering noises fall out of Sam’s mouth as Dean’s throat constricts and his hands pump and explore. Once Sam’s relaxed enough, Dean slides his fingers down, prodding at the pink hole.

“Are – fuck, Dean, are you gonna?”

Popping his mouth off Sam’s dick, Dean purrs back, “Gonna what? What do you want?”

Sam’s thighs spread wide open, which – fuck, such a pretty sight. His ankles dig into Dean’s back.

“Please. Please,” Sam whines. “Fuck me. Want you to fuck me. Want you inside.”

“Gonna get there,” Dean promises, reaching down to push a hand against his hard-as-nails dick. He closes his eyes for a moment, imagining how warm his brother’s going to be inside. His fingers prod a little more while Sam whines for it, and his mouth goes back to sucking, relaxing Sam until he can spread three inside.

The moment he pulls them out, Sam sits up, frantic.

“Wait!” he says, and Dean gets worried for a second, wondering if Sam’s gonna call this off. But Sam pushes forward, fingers reaching down to tug at Dean’s pajama bottoms.

“Wanna suck you first,” he insists. “Let me get you wet.”

Dean complies, lifting up as Sam pulls his pants and underwear off, sighing contentedly when Sam leans down to gulps his dick inside his mouth. It wraps around really pretty, shiny and pink and wet, and Sam’s so enthusiastic, so wet and warm, that Dean has to push him away after just a few seconds.

“Wait, baby,” he says hoarsely, trying to calm the heat throbbing across his body. “Wait. Gonna come, I swear, any second. Wanna get inside that ass first. Been dreaming about it for days.”

“Fuck yeah,” Sam replies softly, flopping back, legs opening back up.

Grateful he’s got it nearby, Dean reaches to the side to flick open the table drawer, slicking his dick up with lube because he wants this to feel good for them both. Sam’s panties are still on, and Dean doesn’t even think about taking them off. It’s too hot this way. He pushes them to the side as he presses in, and Sam’s legs immediately hook around his hips.

“Yeah. _Yeah_ ,” Sam breathes in his ear, arms hooked around Dean’s neck. “Fuck me. Hard, Dean. More. Please. I want it all.”

Dean tucks his head down, feels sweat drip down the side of his face and onto Sam as he pistons in and out, rocking the bed, pushing Sam’s body up and down.

He looks so pretty. Sam’s body is flushed, and Dean quickly pulls off the top so he can feel Sam’s skin-to-skin.

“Am I – am I your dream slut?” Sam asks, breathy and stuttering. He sounds suddenly vulnerable, and Dean opens his eyes, vision blurry because he’s so close, but something about Sam’s tone makes him scrutinize the boy.

He quickly kisses him, several soft quick presses all over his face. Then one long kiss into Sam’s mouth, deep and perfect.

“You’re my dream everything,” he manages before his head goes fuzzy, everything zeroed in on feel and sensation.

His hand gropes for Sam’s dick, sliding it inside his fist and pumping as Dean’s shoves a few more times, deep and hard, feeling every muscle tense as he pushes to that release. Chemicals burst into his brain, flooding every sense with pure pleasure as he comes deep into his brother. Sam takes over his own dick when Dean’s hand goes slack, just two more pumps until Sam’s joining Dean, spurting over his own stomach in long, white ropes.

They both fall to the side, Sam’s hands sliding over Dean’s stomach and Dean reaching to curl an arm around Sam’s shoulders.

They both come back to life slowly, sweat droplets cooling on their skin.

“So, you gonna call me again?” Sam asks slyly against Dean’s shoulder, and he laughs. God, he still doesn’t know what he’s thinking, but Dean selfishly knows he doesn’t want to let this go.

“Hell yeah,” he answers, turning to lightly nuzzle his chin on top of Sam’s head. “Gonna deactivate my account tomorrow. Don’t think anyone else can compare to this night.”

“Yeah?” Sam’s voice is soft, cautious and hopeful.

“Yeah.”


End file.
